Do you know of an easy way to sort and re-number my files?

PC: Picasa. Yes. Actually there are quite a few free programs to sort and renumber photos which are simple, easy-to-use and spyware-free.
The best, prettiest program for sort images is Google's Picasa, which I've provided a link to on Download.com. It's pretty self explanatory, but here's a quick video I just made which shows how to rename your photos using Picasa. You can make the video fullscreen. There's a little toggle at the bottom of the video window.

Mac: use iPhoto. Chances are it came with your Macintosh.

  1. Open iPhoto. Control+click (right-click) on the sidebar and select 'New Album'.  Double click to name it.  Select it.
  2. Select all your images (or a folder containing all your images) and drag into the new, blank window of iPhoto.  You should see them importing.  Good. (if you get a warning about duplicates, just click 'apply to all' so they all import anyways)
  3. Make sure you have your new album selected.  Next, just select your photos, image by image, and drag them into the sort order you want.
  4. When finished, go to Edit > Select All.  Next, go to File > Export...
  5. Size: set to 'Full-size images';  Name:  select 'Use album name', and check 'Use extension.'  Click Export.
  6. That's It.  Make a new folder for the renamed files and click OK.